Used Chevrolet Silverado 1500 Custom Trail Boss for Sale nearNew Point, VA
151 vehicles found
Shop with transparent pricing.
Only show listings that include dealer fees- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 132,858
- Stock #:
- D26062961T1
- VIN:
- 1GCPYCEF8KZ359410
Sponsored by Southern Buick GMC Virginia Beach
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
132,858 mi
Virginia Beach, VA
38 mi away
Fair Deal
$25,494
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Red Hot
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 100,659
- Stock #:
- T01530A
- VIN:
- 1GCPYCEF3MZ206985
New arrival
Sponsored Listing
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
100,659 mi
Norfolk, VA
35 mi away
Fair Deal
$31,478
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Silver
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 143,935
- Stock #:
- 19C2480
- VIN:
- 3GCPYCEF7KG150577
Sponsored Listing
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
143,935 mi
Norfolk, VA
35 mi away
Fair Deal
$23,497
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Shadow Gray Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 56,969
- Stock #:
- 3927
- VIN:
- 1GCRYCEF9KZ249670
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
56,969 mi
Home delivery from Belford, NJ
Price includes $495 shipping
Good Deal
$30,168
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Black
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 51,065
- Stock #:
- 22696A
- VIN:
- 3GCPDCEK3PG106074
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
51,065 mi
Home delivery from Tampa, FL
Price includes $771 shipping
Great Deal
$35,750
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 30,501
- Stock #:
- 7007182A
- VIN:
- 3GCPDCEK1NG607137
Price drop
-$900
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
30,501 mi
Home delivery from Sanford, NC
Price includes $205 shipping
Good Deal
$36,435
$35,535
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- SAND DUNE METALLIC
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 98,341
- Stock #:
- DN680533
- VIN:
- 3GCPDCED9NG680533
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
98,341 mi
Home delivery from Houston, TX
Price includes $1,098 shipping
Fair Deal
$32,703
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Sterling Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 11,005
- Stock #:
- S8846
- VIN:
- 3GCUKCED6SG339563
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
11,005 mi
Home delivery from Salisbury, NC
Price includes $257 shipping
Great Deal
$44,856
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Summit White
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 53,803
- Stock #:
- PM174391
- VIN:
- 1GCPYCEL0NZ174391
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
53,803 mi
Home delivery from Pleasantville, NJ
Price includes $444 shipping
Great Deal
$35,679
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Exterior color:
- Red Hot
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 49,453
- Stock #:
- ZC26344
- VIN:
- 1GCPYCEK2NZ120128
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
49,453 mi
Home delivery from Hicksville, OH
Price includes $660 shipping
Great Deal
$32,570
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 17 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 62,855
- Stock #:
- 6629730A
- VIN:
- 3GCUDCED8RG264868
New arrival
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,855 mi
Home delivery from Lexington, TN
Price includes $1,705 shipping
Fair Deal
$41,672
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Silver
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 143,935
- Stock #:
- 19C2480
- VIN:
- 3GCPYCEF7KG150577
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
143,935 mi
Norfolk, VA
35 mi away
Fair Deal
$23,497
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Blue
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Black
- Transmission:
- Automatic
- Mileage:
- 68,312
- Stock #:
- Z206955
- VIN:
- 1GCRYCEF6LZ206955
New arrival
2020 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
68,312 mi
Home delivery from Houston, TX
Price includes $1,836 shipping
Fair Deal
$32,756
- Year:
- 2025
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Cypress Gray
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 34,640
- Stock #:
- T2443A
- VIN:
- 3GCPKCEK1SG189857
2025 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
34,640 mi
Home delivery from Charlottesville, VA
Price includes $202 shipping
Good Deal
$41,074
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gray
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 62,775
- Stock #:
- 5019
- VIN:
- 1GCPYCEF0LZ168095
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,775 mi
Home delivery from Burton, MI
Price includes $551 shipping
Great Deal
$29,551
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Ash
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,423
- Stock #:
- CU96161
- VIN:
- 3GCPDCEK7PG275630
Price drop
-$1,535
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,423 mi
Newport News, VA
22 mi away
Good Deal
$40,562
$39,027
- Year:
- 2022
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Glacier Blue Metallic
- Combined gas mileage:
- 18 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 82,773
- Stock #:
- 54173
- VIN:
- 3GCPDCEK6NG533147
2022 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
82,773 mi
Home delivery from Cambridge, OH
Price includes $256 shipping
Fair Deal
$31,534
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Northsky Blue Metallic
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 69,041
- Stock #:
- K26986A
- VIN:
- 1GCRYCEF8KZ326786
2019 Chevrolet Silverado 1500
Custom Trail Boss Double Cab 4WD
69,041 mi
Home delivery from Ashland, KY
Price includes $1,068 shipping
Fair Deal
$30,352
- Year:
- 2024
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Sterling Gray Metallic
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 15,445
- Stock #:
- J260616147T1
- VIN:
- 3GCPDCEK1RG309158
2024 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
15,445 mi
Chesapeake, VA
35 mi away
Good Deal
$42,917
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Summit White
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 62,366
- Stock #:
- 6R188A
- VIN:
- 1GCPYCEF6MZ353642
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
62,366 mi
Williamsburg, VA
25 mi away
Fair Deal
$36,689
- Year:
- 2019
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Gideon/Very Dark Atmosphere
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 115,088
- Stock #:
- 144370
- VIN:
- 1GCPYCEF5KZ345870
2019 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
115,088 mi
Home delivery from Fredericksburg, VA
Price includes $152 shipping
Fair Deal
$28,636
- Year:
- 2021
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Black
- Combined gas mileage:
- 15 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- Automatic
- Mileage:
- 65,619
- Stock #:
- T01414A
- VIN:
- 3GCPYCEF3MG481434
2021 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
65,619 mi
Norfolk, VA
35 mi away
Fair Deal
$36,886
- Year:
- 2020
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 355 hp 5.3L V8
- Exterior color:
- Summit White
- Combined gas mileage:
- 16 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 6-Speed Automatic Overdrive
- Mileage:
- 85,119
- Stock #:
- 181899
- VIN:
- 3GCPYCEF6LG181899
2020 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
85,119 mi
Home delivery from South Boston, VA
Price includes $155 shipping
Fair Deal
$30,948
- Year:
- 2023
- Make:
- Chevrolet
- Model:
- Silverado 1500
- Body type:
- Pickup Truck
- Doors:
- 4 doors
- Drivetrain:
- Four-Wheel Drive
- Engine:
- 310 hp 2.7L I4
- Exterior color:
- Ash
- Combined gas mileage:
- 19 MPG
- Fuel type:
- Gasoline
- Interior color:
- Jet Black
- Transmission:
- 8-Speed Automatic
- Mileage:
- 35,423
- Stock #:
- CU96161
- VIN:
- 3GCPDCEK7PG275630
Price drop
-$1,535
Sponsored Listing
2023 Chevrolet Silverado 1500
Custom Trail Boss Crew Cab 4WD
35,423 mi
Newport News, VA
22 mi away
Good Deal
$40,562
$39,027
FAQs
How much does the Chevrolet Silverado 1500 Custom Trail Boss cost in New Point, VA?
The average Chevrolet Silverado 1500 Custom Trail Boss costs about $27,080.70. The average price has decreased by -0.4% since last year. The 151 for sale near New Point, VA on CarGurus, range from $22,712 to $65,941 in price.
How many Chevrolet Silverado 1500 Custom Trail Boss vehicles in New Point, VA have no reported accidents or damage?
149 out of 151 for sale near New Point, VA have no reported accidents or damage.
What is the fuel economy of the Chevrolet Silverado 1500 Custom Trail Boss?
Depending on the engine and options, the Chevrolet Silverado 1500 Custom Trail Boss gets between 15 and 24 MPG (or EV battery range).
What fuel types are available?
Diesel, Flex Fuel Vehicle, Gasoline engines are available.
Relevant articles
Craig Fitzgerald
The Best Trucks Under $25,000 in 2026
New trucks cost more than ever, but the prices of used ones finally seem to be cooling. You still can't find the latest and fanciest full-sizes for budget prices, but fortunately, there are plenty of good trucks under $25,000 these days. Here, we've assembled a list of the best.
Craig Fitzgerald
The Best Cars to Tow Behind an RV in 2026
Not many new models can be towed behind an RV. We’ve identified several that are recommended for flat-towing according to their owner’s manual, and a few used models that have fewer technological or engineering restrictions.
CarGurus Editorial Team
Car Deals with 0% APR in July 2026
Our experts have tracked down the latest 0% APR car deals, as well as examined the pros and cons of interest-free car loans versus other financing options.
Chevrolet Silverado 1500 LT in New Point VAChevrolet Silverado 1500 RST in New Point VAChevrolet Silverado 1500 LTZ in New Point VAChevrolet Silverado 1500 LT Trail Boss in New Point VAChevrolet Silverado 1500 LT1 in New Point VAChevrolet Silverado 1500 Custom in New Point VAChevrolet Silverado 1500 High Country in New Point VAChevrolet Silverado 1500 Custom Trail Boss in New Point VAChevrolet Silverado 1500 Work Truck in New Point VA
Chevrolet Silverado 1500 in Williamsburg VAChevrolet Silverado 1500 in Norfolk VAChevrolet Silverado 1500 in Richmond VAChevrolet Silverado 1500 in Elizabeth City NCChevrolet Silverado 1500 in Salisbury MDChevrolet Silverado 1500 in Fredericksburg VAChevrolet Silverado 1500 in Washington DCChevrolet Silverado 1500 in Manassas VAChevrolet Silverado 1500 in Rocky Mount NC
Chevrolet Silverado 1500 in New Point VAOld Chevy Trucks for Sale in New Point VAClassic Muscle Cars for Sale in New Point VAChevrolet Trucks For Sale in New Point VACheap Muscle Cars for Sale in New Point VAWork Trucks for Sale in New Point VAReliable Cars For Sale in New Point VAAmerican Made Trucks For Sale in New Point VABest Pickup Trucks For Sale in New Point VABest Cars Under $5,000 For Sale in New Point VA
All Used CarsManual Transmission CarsLuxury CarsCars with Red InteriorCheap Manual CarsHybrid CarsSports CarsElectric SUVsCheap TrucksSmall CarsThird Row SUVsThree Quarter Ton TrucksLifted TrucksManual Transmission TrucksDiesel TrucksHybrid SUVsDually TrucksOne Ton TrucksCheap SUVsLifted Ford Trucks4x4 TrucksWork TrucksAWD SUVsFord TrucksChevrolet TrucksToyota TrucksTrucks Under $10,000Cars Under $15,000Sports Cars Under $20,000Trucks Under $20,000Used Sedans for Sale with Low Mileage in New PointUsed SUVs / Crossovers for Sale with Low Mileage in New PointUsed Hatchbacks for Sale with Low Mileage in New PointUsed Convertibles for Sale with Low Mileage in New PointUsed Vans for Sale with Low Mileage in New PointUsed Minivans for Sale with Low Mileage in New PointUsed Pickup Trucks for Sale with Low Mileage in New PointUsed Coupes for Sale with Low Mileage in New PointUsed Wagons for Sale with Low Mileage in New Point
